Carbon Tetrachloride → 1227370-64-0

Triphenylphosphine (5.71 g, 21.8 mmol), carbon tetrachloride (8.4 mL, 87 mmol), and tetrahydrofuran (12 mL) were combined in a round bottom flask under argon and stirred at room temperature for 10 minutes. A heterogeneous mixture of (4-methanesulfonylmethyl-phenyl)-methanol (2.18 g, 10.9 mmol) and tetrahydrofuran (37 mL) were added to the reaction mixture, and then the mixture was heated at 75° C. for 3 hours. The reaction mixture was cooled to room temperature, and then partitioned between ethyl acetate and water. The organic phase was dried over MgSO4, filtered, and concentrated to give the crude product as an oily solid. A solution of this crude product and dichloromethane was concentrated over silica gel, and the resulting silica gel supported crude product was loaded onto a RediSep® Flash column. Flash chromatography (25%-40% ethyl acetate in hexanes) afforded 1.59 g (67%) of 1-chloromethyl-4-methanesulfonylmethyl benzene as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.47 (d, J=8.2 Hz, 2 H), 7.41 (d, J=8.2 Hz, 2 H), 4.78 (s, 2 H), 4.50 (s, 2 H), 2.91 (s, 3 H).

1. additionwere added to the reaction mixture
2. temperaturethe mixture was heated at 75° C. for 3 hours
3. temperatureThe reaction mixture was cooled to room temperature
4. custompartitioned between ethyl acetate and water
5. dry with materialThe organic phase was dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customto give the crude product as an oily solid
9. concentrationA solution of this crude product and dichloromethane was concentrated over silica gel

ORD record

ord-194e5e3e0ebe49e6a471b7d41896bbb3

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124629B2